1,2-Epoxypentyl 4-nitrobenzoate | 292601-60-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,2-Epoxypentyl 4-nitrobenzoate
• 英文别名: 3-(Oxiran-2-yl)propyl 4-nitrobenzoate
• CAS: 292601-60-6
• 化学式: C₁₂H₁₃NO₅
• 分子量: 251.239
• InChiKey: CSRPAVLCSRAPFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  84.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,2-Epoxypentyl 4-nitrobenzoate 在 5percent Pd/C(en) 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以100%的产率得到1,2-Epoxypentyl 4-aminobenzoate
  参考文献：
  名称：

  Highly Chemoselective Hydrogenation with Retention of the Epoxide Function Using a Heterogeneous Pd/C-Ethylenediamine Catalyst and THF

  摘要：

  In general, palladium-carbon (Pd/C) catalyzed hydrogenation of epoxides affords the corresponding primary and secondary alcohols as a mixture. It has been found that the catalytic activity of a Pd/C -ethylenediamine complex catalyst [Pd/C(en)] in the hydrogenolysis of epoxide functions is drastically reduced. Herein we describe a mild and chemoselective method for the hydrogenation of olefin, nitro, and azide functions with retention of the epoxide function. The chemoselectivity was accomplished by using a combination of 5% Pd/C(en) and THF as solvent. A significant drop in the chemoselectivity of the hydrogenation is observed with 5% Pd/C(en) in MeOH. These results reinforce the utility of epoxides as important precursors of alcohols in synthetic chemistry.

  DOI：

  10.1002/1521-3765(20000616)6:12<2200::aid-chem2200>3.0.co;2-3
• 作为产物：
  描述：

  4-Pentenyl 4-nitrobenzoate 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 以86%的产率得到1,2-Epoxypentyl 4-nitrobenzoate
  参考文献：
  名称：

  Highly Chemoselective Hydrogenation with Retention of the Epoxide Function Using a Heterogeneous Pd/C-Ethylenediamine Catalyst and THF

  摘要：

  In general, palladium-carbon (Pd/C) catalyzed hydrogenation of epoxides affords the corresponding primary and secondary alcohols as a mixture. It has been found that the catalytic activity of a Pd/C -ethylenediamine complex catalyst [Pd/C(en)] in the hydrogenolysis of epoxide functions is drastically reduced. Herein we describe a mild and chemoselective method for the hydrogenation of olefin, nitro, and azide functions with retention of the epoxide function. The chemoselectivity was accomplished by using a combination of 5% Pd/C(en) and THF as solvent. A significant drop in the chemoselectivity of the hydrogenation is observed with 5% Pd/C(en) in MeOH. These results reinforce the utility of epoxides as important precursors of alcohols in synthetic chemistry.

  DOI：

  10.1002/1521-3765(20000616)6:12<2200::aid-chem2200>3.0.co;2-3

文献信息

• Highly Chemoselective Hydrogenation with Retention of the Epoxide Function Using a Heterogeneous Pd/C-Ethylenediamine Catalyst and THF
  作者：Hironao Sajiki、Kazuyuki Hattori、Kosaku Hirota

  DOI：10.1002/1521-3765(20000616)6:12<2200::aid-chem2200>3.0.co;2-3

  日期：2000.6.16

  In general, palladium-carbon (Pd/C) catalyzed hydrogenation of epoxides affords the corresponding primary and secondary alcohols as a mixture. It has been found that the catalytic activity of a Pd/C -ethylenediamine complex catalyst [Pd/C(en)] in the hydrogenolysis of epoxide functions is drastically reduced. Herein we describe a mild and chemoselective method for the hydrogenation of olefin, nitro, and azide functions with retention of the epoxide function. The chemoselectivity was accomplished by using a combination of 5% Pd/C(en) and THF as solvent. A significant drop in the chemoselectivity of the hydrogenation is observed with 5% Pd/C(en) in MeOH. These results reinforce the utility of epoxides as important precursors of alcohols in synthetic chemistry.